CA2005241C - Uv-crosslinkable materials based on (meth) acrylate polymers - Google Patents

Uv-crosslinkable materials based on (meth) acrylate polymers Download PDF

Info

Publication number: CA2005241C
Authority: CA; Canada
Prior art keywords: radical; meth; alkyl; acrylate; weight
Prior art date: 1988-12-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002005241A

Other languages

English (en)

French (fr)

Other versions

CA2005241A1 (en

Inventor

Gerg Rehmer

Andreas Boettcher

Gerhard Auchter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-12-31

Filing date

1989-12-12

Publication date

2000-02-01

1989-12-12 Application filed by BASF SE filed Critical BASF SE

1990-06-30 Publication of CA2005241A1 publication Critical patent/CA2005241A1/en

2000-02-01 Application granted granted Critical

2000-02-01 Publication of CA2005241C publication Critical patent/CA2005241C/en

2009-12-12 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims abstract description 24
229920000058 polyacrylate Polymers 0.000 title description 4
229920001577 copolymer Polymers 0.000 claims abstract description 52
239000000178 monomer Substances 0.000 claims abstract description 35
239000002253 acid Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
150000001450 anions Chemical class 0.000 claims abstract description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims abstract description 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 4
125000006850 spacer group Chemical group 0.000 claims abstract description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 21
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229920005989 resin Polymers 0.000 claims description 4
239000011347 resin Substances 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
-1 alkyl radical Chemical class 0.000 abstract description 34
150000003254 radicals Chemical class 0.000 abstract description 16
229930195733 hydrocarbon Natural products 0.000 abstract description 4
150000002430 hydrocarbons Chemical class 0.000 abstract description 4
239000004215 Carbon black (E152) Substances 0.000 abstract 1
206010011416 Croup infectious Diseases 0.000 abstract 1
150000005840 aryl radicals Chemical class 0.000 abstract 1
201000010549 croup Diseases 0.000 abstract 1
239000000203 mixture Substances 0.000 description 27
229940117913 acrylamide Drugs 0.000 description 20
238000000576 coating method Methods 0.000 description 17
150000001252 acrylic acid derivatives Chemical class 0.000 description 16
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
150000008366 benzophenones Chemical class 0.000 description 13
238000000034 method Methods 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000004821 Contact adhesive Substances 0.000 description 12
239000000853 adhesive Substances 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
239000002904 solvent Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
230000005855 radiation Effects 0.000 description 11
238000012360 testing method Methods 0.000 description 11
230000001070 adhesive effect Effects 0.000 description 10
229940063557 methacrylate Drugs 0.000 description 10
239000000155 melt Substances 0.000 description 9
239000004831 Hot glue Substances 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
239000011248 coating agent Substances 0.000 description 8
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
150000002734 metacrylic acid derivatives Chemical class 0.000 description 8
238000006116 polymerization reaction Methods 0.000 description 8
230000008569 process Effects 0.000 description 8
239000000758 substrate Substances 0.000 description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000003505 polymerization initiator Substances 0.000 description 5
ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
239000012965 benzophenone Substances 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
229910000831 Steel Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
229940024874 benzophenone Drugs 0.000 description 3
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000005259 measurement Methods 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
239000010959 steel Substances 0.000 description 3
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
150000008062 acetophenones Chemical class 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
150000003926 acrylamides Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
238000012662 bulk polymerization Methods 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
238000013016 damping Methods 0.000 description 2
230000032798 delamination Effects 0.000 description 2
125000004386 diacrylate group Chemical group 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
230000000622 irritating effect Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000005385 peroxodisulfate group Chemical group 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000007789 sealing Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
HGKYIVYFGFLSLO-UHFFFAOYSA-N (2-methyloxolan-2-yl) prop-2-enoate Chemical compound C=CC(=O)OC1(C)CCCO1 HGKYIVYFGFLSLO-UHFFFAOYSA-N 0.000 description 1
WQJUBZMZVKITBU-UHFFFAOYSA-N (3,4-dimethyl-4-phenylhexan-3-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(CC)C(C)(CC)C1=CC=CC=C1 WQJUBZMZVKITBU-UHFFFAOYSA-N 0.000 description 1
FSQQTNAZHBEJLS-OWOJBTEDSA-N (e)-4-amino-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C\C(O)=O FSQQTNAZHBEJLS-OWOJBTEDSA-N 0.000 description 1
XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
GJRCLMJHPWCJEI-UHFFFAOYSA-N 1,9-Nonanedithiol Chemical compound SCCCCCCCCCS GJRCLMJHPWCJEI-UHFFFAOYSA-N 0.000 description 1
UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
HBKBEZURJSNABK-MWJPAGEPSA-N 2,3-dihydroxypropyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)OCC(O)CO HBKBEZURJSNABK-MWJPAGEPSA-N 0.000 description 1
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
NQOGBCBPDVTBFM-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)COC(C)CO NQOGBCBPDVTBFM-UHFFFAOYSA-N 0.000 description 1
QUASZQPLPKGIJY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOCCOC(=O)C=C QUASZQPLPKGIJY-UHFFFAOYSA-N 0.000 description 1
PLWQJHWLGRXAMP-UHFFFAOYSA-N 2-ethenoxy-n,n-diethylethanamine Chemical compound CCN(CC)CCOC=C PLWQJHWLGRXAMP-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
SZFABAXZLWVKDV-UHFFFAOYSA-N 2-methyloctanoyl 2-methyloctaneperoxoate Chemical compound CCCCCCC(C)C(=O)OOC(=O)C(C)CCCCCC SZFABAXZLWVKDV-UHFFFAOYSA-N 0.000 description 1
CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
BXBBQMFWCACOBG-UHFFFAOYSA-N 3,3-dihydroxypropyl prop-2-enoate Chemical class OC(O)CCOC(=O)C=C BXBBQMFWCACOBG-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 description 1
DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
- Y10S522/905—Benzophenone group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Adhesives Or Adhesive Processes (AREA)
Paints Or Removers (AREA)
Macromonomer-Based Addition Polymer (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Graft Or Block Polymers (AREA)

CA002005241A 1988-12-31 1989-12-12 Uv-crosslinkable materials based on (meth) acrylate polymers Expired - Fee Related CA2005241C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3844445A DE3844445A1 (de)	1988-12-31	1988-12-31	Uv-vernetzbare massen auf basis von (meth)-acrylesterpolymerisaten
DEP3844445.3		1988-12-31

Publications (2)

Publication Number	Publication Date
CA2005241A1 CA2005241A1 (en)	1990-06-30
CA2005241C true CA2005241C (en)	2000-02-01

Family

ID=6370611

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002005241A Expired - Fee Related CA2005241C (en)	1988-12-31	1989-12-12	Uv-crosslinkable materials based on (meth) acrylate polymers

Country Status (10)

Country	Link
US (1)	US5128386A (de)
EP (1)	EP0377199B1 (de)
JP (1)	JP2846014B2 (de)
KR (1)	KR0139625B1 (de)
AT (1)	ATE89837T1 (de)
AU (1)	AU619069B2 (de)
CA (1)	CA2005241C (de)
DE (2)	DE3844445A1 (de)
ES (1)	ES2055002T3 (de)
FI (1)	FI98921C (de)

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1989
- 1989-12-07 FI FI895843A patent/FI98921C/fi not_active IP Right Cessation
- 1989-12-12 CA CA002005241A patent/CA2005241C/en not_active Expired - Fee Related
- 1989-12-15 US US07/451,085 patent/US5128386A/en not_active Expired - Lifetime
- 1989-12-27 DE DE8989123926T patent/DE58904500D1/de not_active Expired - Lifetime
- 1989-12-27 ES ES89123926T patent/ES2055002T3/es not_active Expired - Lifetime
- 1989-12-27 JP JP1336746A patent/JP2846014B2/ja not_active Expired - Lifetime
- 1989-12-27 AT AT89123926T patent/ATE89837T1/de not_active IP Right Cessation
- 1989-12-27 EP EP89123926A patent/EP0377199B1/de not_active Expired - Lifetime
- 1989-12-29 AU AU47337/89A patent/AU619069B2/en not_active Expired
1990
- 1990-01-03 KR KR1019900000045A patent/KR0139625B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ATE89837T1 (de)	1993-06-15
FI895843A0 (fi)	1989-12-07
KR0139625B1 (ko)	1998-07-01
DE58904500D1 (de)	1993-07-01
JP2846014B2 (ja)	1999-01-13
US5128386A (en)	1992-07-07
DE3844445A1 (de)	1990-07-19
FI98921B (fi)	1997-05-30
EP0377199A3 (de)	1991-03-20
EP0377199B1 (de)	1993-05-26
FI98921C (fi)	1997-09-10
AU619069B2 (en)	1992-01-16
ES2055002T3 (es)	1994-08-16
CA2005241A1 (en)	1990-06-30
EP0377199A2 (de)	1990-07-11
KR910014411A (ko)	1991-08-31
JPH02229810A (ja)	1990-09-12
AU4733789A (en)	1990-07-05

Legal Events

Date	Code	Title	Description
1996-06-14	EEER	Examination request
2007-12-12	MKLA	Lapsed

Publication	Publication Date	Title
CA2005241C (en)	2000-02-01	Uv-crosslinkable materials based on (meth) acrylate polymers
US5264533A (en)	1993-11-23	Benzophenone derivatives and their preparation
CA1337615C (en)	1995-11-21	Benzophenone derivatives and their preparation
US5026806A (en)	1991-06-25	UV-crosslinkable materials based on isoamyl (meth)acrylate copolymers
US5073611A (en)	1991-12-17	Copolymers crosslinkable by ultraviolet radiation in the atmosphere
JP2925314B2 (ja)	1999-07-28	シリコーン化エマルジョンを主材とする感圧接着剤
US5294688A (en)	1994-03-15	UV-crosslinkable copolymers
CA1335020C (en)	1995-03-28	Hotmelt contact adhesives which can be crosslinked with ultraviolet radiation in the air
US5180756A (en)	1993-01-19	Agents curable by ultraviolet radiation
MXPA97008641A (en)	1998-02-01	Adhesives sensitive to pressure, based on acrylic, pigmented, cured with ultraviolet radiation, and method for the manufacture of mis
EP3137523A1 (de)	2017-03-08	Physikalisch vernetzbares haftendes copolymer
US7091296B2 (en)	2006-08-15	UV-crosslinkable copolymers
US8871827B2 (en)	2014-10-28	Hotmelt adhesive comprising radiation-crosslinkable poly(meth)acrylate and oligo(meth)acrylate with nonacrylic C-C double bonds
CA1336628C (en)	1995-08-08	Radiation-crosslinkable contact adhesive mixtures
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